The visible and NIR maximum degree of polarization (DoP) of cloud-free skylight depends on many factors, including wavelength, sun zenith angle, surface reflectance, and aerosol properties. For clear-sky environments, radiative transfer models accurately estimate the sky DoP when each of these properties is well constrained. (The model used here was recently compared with full-sky polarization measurements with excellent agreement.) Using coincident Hyperion satellite observations and AERONET retrievals to provide model inputs, we simulate the maximum sky DoP for a variety of locations. Results show large variations in the wavelength dependence of sky polarization across different Earth environments. Therefore, accurate modeling of the sky DoP depends largely upon proper representation of the surface and aerosols in the model. Simple models which do not incorporate accurate aerosol and surface information have limited utility for simulating cloud-free sky DoP.